DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Election/Restrictions
Applicant’s election without traverse of Group I (Claims 1-9) in the reply filed on 29 December 2025 is acknowledged.
Claims 10-14 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 29 December 2025.
Claims 1-9, submitted on 17 August 2023, represent all claims currently under consideration.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
The effective filing date is 23 November 2021.
Information Disclosure Statement
Seven Information Disclosure Statements (IDSs), submitted on 17 August 2023, 18 August 2023, 19 September 2024, 16 January 2025, 18 March 2025 (2), and 28 August 2025, are acknowledged and have been considered. The information disclosure statement filed 18 March 2025 fails to comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609 because there are no English translations provided for the Korean Office Action or the Japanese Notice of Allowance. It has been placed in the application file, but the information referred to therein has not been considered as to the merits. Applicant is advised that the date of any re-submission of any item of information contained in this information disclosure statement or the submission of any missing element(s) will be the date of submission for purposes of determining compliance with the requirements based on the time of filing the statement, including all certification requirements for statements under 37 CFR 1.97(e). See MPEP § 609.05(a).
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 4 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Claim 4 is indefinite because it is unclear from the definition of X (at least one selected from the group consisting of…) if the compounds of Chemical Formula I can have more than one metal as part of the formula, i.e. if a compound of Chemical Formula I can be (Ni-Fe)(O-R)a, or other complexes with more than one metal.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-9 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (KR 20000051813; Publication Date: 16 August 2000) in view of Mitsubishi Chemical Corp (JP H0959224; Publication Date: 4 March 1997) and Martyanov (Applied Catalysis A: General, 339, 1, 2008, 45-52).
Kim (See IDS, 17 August 2023) discloses a process for preparing asymmetric linear carbonate esters by transesterification in the presence of a catalyst with two different symmetrical linear carbonate esters, using an alkoxide salt of Group IA element as the reaction catalyst (Claim 1). Claim 2 claims the method of claim 1 wherein the symmetric linear carbonate comprises two different selected from the group consisting of dimethyl carbonate, diethyl carbonate, dipropyl carbonate, and dibutyl carbonate. The amount of catalyst used is 0.0001 to 5% by weight, preferably 0.01 to 1% by weight of catalyst regardless of the kind of reactor used for the reaction (Page 5). No particular limitation is placed on the molar ratio between the two different symmetrical linear carbonic acid esters that are starting materials, and it is preferable to focus on obtaining the maximum yield of the final product asymmetric linear carbonic acid ester. Usually from 10:1 to 1:10, and reacting in different, but equivalent molar ratios depending on the starting materials, are advantageous in terms of productivity (Page 5). Further, the reaction temperature is not particularly limited, but it is preferable to react at a temperature adjacent to the boiling point of the reactant and more preferably 40°-200°C. This is because when the reaction temperature is less than 40°C, the production rate of the final product is slow, and when the temperature exceeds 200°C, decomposition of reactants and production of by products is high, resulting in undesirable properties (Page 5). After the reaction, the reaction mixture is separated from the unreacted symmetrical linear carbonic acid ester by a distillation method such as pressure, atmospheric pressure, or reduced pressure (Page 5). Example 1 provides an example where 10 moles of dimethyl carbonate and 10 moles of diethyl carbonate were reacted with LiOCH, and heated to 110°C.
Kim does not disclose the use of the claimed metal alkoxides in the transesterification reaction.
Mitsubishi Chemical Corp (See IDS, 17 August 2023) provides a method for efficiently and industrially producing an alkylaryl carbonate in high purity. The alkylaryl carbonate is separated by distillation from the reaction mixture obtained by the transesterification reaction of the dialkyl carbonate with the diaryl carbonate and the other fractions and distillation residue are recycled to the transesterification reaction system (Abstract). Specific examples of alkyl carbonates include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, t-butyl, and methylcyclopropyl. Dimethyl carbonate and diethylcarbonate are particularly preferred (Paragraph 0010). In the transesterification reaction of the present invention, the molar ratio of the dialkyl carbonate to the diaryl carbonate is theoretically 1:1, but is not limited thereto and can be used in a wide range, and is usually in the range of 1:20 to 20:1, preferably 3:1 to 1:3. The reaction temperature is usually in the range of 30 to 300°C, preferably 50 to 200°C (Paragraph 0017). Any catalyst may be used as long as it is generally used for transesterification. Examples include inorganic acids, alkoxides of alkyl metals or alkaline earth metals, alkoxides or halides of transition metals such as iron, tin, cobalt, and vanadium, and compounds of molybdenum, bismuth, tellurium, scandium, manganese, and zirconium (Paragraph 0018). Among these catalysts, an alkoxide or halide of a transition metal, and a compound of molybdenum, bismuth, tellurium, scandium, manganese, and zirconium are preferable. The amount of catalysts to be used varies depending on the kind of the catalysts to be used, but is 1-50000 ppm in the reactant solution (Paragraph 0019). It is not always necessary to use a solvent (Paragraph 0020). The target product can be obtained by distillation of the reaction mixture, or after separating the catalyst by filtration, centrifugation, or the like (Paragraph 0021).
Martyanov discloses the catalytic activity of magnesium and calcium methoxides (Mg(OCH3)2 and Ca(OCH3)2) in the transesterification of tributyrine (Abstract).
Kim, Mitsubishi, and Martyanov are considered analogous to the claimed invention as all are involved in performing transesterification reactions. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify the method of producing asymmetric linear carbonates disclosed by Kim by replacing the catalysts of Kim with the metal alkoxide catalysts of Mitsubishi, such as alkoxides of iron, tin, cobalt, vanadium, or compounds of molybdenum, tellurium scandium, manganese, or zirconium, to arrive at the claimed invention. Martyanov demonstrates that other metal alkoxides, such as calcium dimethoxide and magnesium dimethoxide are useful as catalysts in transesterification reactions. The substitution of the catalysts of Kim with the specific metal alkoxides claimed in this invention, as taught by Mitsubishi and Martyanov, is prima facie obvious simple substitution of one known element for another to obtain predictable results (See MPEP § 2143 I (B)); the catalysts claimed in the examined application are known in the art to be useful for similar transesterification reactions, as shown by both Mitsubishi and Martyanov, and the artisan would recognize this, and have a reasonable expectation of success in performing this substitution. Moreover, the selection of the specific metal alkoxide catalysts of Claim 5 is prima facie obvious substitution of an equivalent known for the same purpose (See MPEP § 2144.06 II); Martyanov shows that calcium methoxide and magnesium dimethoxide are both useful in transesterification processes, and thus, it would be obvious to use these catalysts in the claimed transesterification reaction.
Claims 1-9 are rejected under 35 U.S.C. 103 as being unpatentable over Gan (EP 0885874; Publication Date: 23 December 1998) in view of Mitsubishi Chemical Corp (JP H0959224; Publication Date: 4 March 1997) and Martyanov (Applied Catalysis A: General, 339, 1, 2008, 45-52).
Gan discloses a method of synthesizing unsymmetric linear organic carbonates comprising the reaction of two symmetric dialkyl carbonates in the presence of a nucleophilic reagent or an electron donating reductant as a catalyst (Abstract). The two symmetric dialkyl carbonates are reacted in the presence of a nucleophilic reagent or electron donating reductant as a catalyst, wherein R1 and R2 can be either saturated or unsaturated alkyl or aryl groups. The two symmetric dialkyl carbonates are preferably present in the starting reaction mixture in a molar ratio of about 9:1 to 1:9
PNG
media_image1.png
65
572
media_image1.png
Greyscale
(Page 3, Lines 15-19). At least two types of catalysts are able to initiate the ester exchange reaction of the present invention, namely, a nucleophilic reagent such as an alkoxide and an amide, an organic or aryl anion and an electron donating reductant inlcuding an alkali metal such as lithium, an alkalated carbon such as lithiated carbon and a samarium salt. Suitable nucleophilic reagents include lithium dialkylamide, lithium alkoxide, an alkyl lithium, and an aryl lithium (Page 3, Lines 38-46). The catalyst is easily separated from the reaction mixture by filtration through a column of alumina or silica gel. After removing the catalyst, the product is readily purified by utilizing commonly known separation techniques such as vacuum distillation, normal pressure distillation, high pressure distillation, extraction, crystallization, chromatography, and the like (Page 3, Lines 54-57).
Gan does not disclose the use of the claimed metal alkoxides in the transesterification reaction.
The teachings of Mitsubishi and Martyanov are previously described and are fully incorporated into this rejection.
Gan, Mitsubishi, and Martyanov are considered analogous to the claimed invention as all are involved in performing transesterification reactions. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify the method of producing asymmetric linear carbonates disclosed by Gan by replacing the catalysts of Gan with the metal alkoxide catalysts of Mitsubishi, such as alkoxides of iron, tin, cobalt, vanadium, or compounds of molybdenum, tellurium scandium, manganese, or zirconium, to arrive at the claimed invention. Martyanov demonstrates that other metal alkoxides, such as calcium dimethoxide and magnesium dimethoxide are useful as catalysts in transesterification reactions. The substitution of the catalysts of Gan with the specific metal alkoxides claimed in this invention, as taught by Mitsubishi and Martyanov, is prima facie obvious simple substitution of one known element for another to obtain predictable results (See MPEP § 2143 I (B)); the catalysts claimed in the examined application are known in the art to be useful for similar transesterification reactions, as shown by both Mitsubishi and Martyanov, and the artisan would recognize this, and have a reasonable expectation of success in performing this substitution. Moreover, the selection of the specific metal alkoxide catalysts of Claim 5 is prima facie obvious substitution of an equivalent known for the same purpose (See MPEP § 2144.06 II); Martyanov shows that calcium methoxide and magnesium dimethoxide are both useful in transesterification processes, and thus, it would be obvious to use these catalysts in the claimed transesterification reaction.
Conclusion
Claims 1-9 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PHILLIP MATTHEW RZECZYCKI whose telephone number is (703)756-5326. The examiner can normally be reached Monday Thru Friday 730AM-5PM EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Andrew Kosar can be reached at 571-272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/P.M.R./Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625